I grew out my hair during the beginning of my sophomore year in high school (at longest, it was down to the middle of my back). I just recently graduated from high school this past June and I finally cut my hair later that same month. Now my hair is at medium length with side-swept bangs. While I liked long hair (I'm a drummer and a fan of metal music), it became difficult to manage. Also my hair was just one length (now its layered and looks much better). Sometimes, I do miss those days, but I really like my hairstyle now. My hair dries faster and looks better on me. Not to mention it feels so much lighter now.
I have long hair right now (Down to my waist.) and I'm planning on cutting it when I turn 18 so it's easier when I join the Army. (I'm still considering that.) So about 2 years from now. I've had friends who had long hair and then cut it. They all miss it, but they don't miss the hard work that came with taking care of it. Also, it's lighter.
I'd say take it slow. Maybe cut off 2-3 inches every week. That way you have a little while to get used to it and are 100% sure you want to cut it. Then when it finally IS short enough you can cut it to the style you want without instantly missing it. You have time to back out if you want. Just go slow.
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